NL8201290A - Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. - Google Patents
Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. Download PDFInfo
- Publication number
- NL8201290A NL8201290A NL8201290A NL8201290A NL8201290A NL 8201290 A NL8201290 A NL 8201290A NL 8201290 A NL8201290 A NL 8201290A NL 8201290 A NL8201290 A NL 8201290A NL 8201290 A NL8201290 A NL 8201290A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- reaction
- group
- carbon atoms
- compound
- Prior art date
Links
- ZBVZOMFYISPWMD-UHFFFAOYSA-N amino thiohypochlorite Chemical class NSCl ZBVZOMFYISPWMD-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 35
- 239000002917 insecticide Substances 0.000 title description 8
- 239000000642 acaricide Substances 0.000 title description 3
- 239000005645 nematicide Substances 0.000 title description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 7
- 230000001069 nematicidal effect Effects 0.000 claims abstract description 5
- 230000003129 miticidal effect Effects 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 60
- -1 amine compound Chemical class 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000007514 bases Chemical class 0.000 claims description 18
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical class NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical class NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 claims 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229940086542 triethylamine Drugs 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 6
- VFTCEPBUNAKJHC-UHFFFAOYSA-N [acetyloxy(ethyl)amino] acetate Chemical compound CC(=O)ON(CC)OC(C)=O VFTCEPBUNAKJHC-UHFFFAOYSA-N 0.000 description 5
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 3
- 150000005826 halohydrocarbons Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OZCPYLRDULGVFK-UHFFFAOYSA-N ethyl 2-[chlorosulfanyl-(2-ethoxy-2-oxoethyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)CC(=O)OCC OZCPYLRDULGVFK-UHFFFAOYSA-N 0.000 description 2
- AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- VXGABWCSZZWXPC-UHFFFAOYSA-N methyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 description 2
- XTFWRKOFYMGGRB-UHFFFAOYSA-N methyl 2-[chlorosulfanyl-(2-methoxy-2-oxoethyl)amino]acetate Chemical compound COC(=O)CN(SCl)CC(=O)OC XTFWRKOFYMGGRB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- RSNAEYGESKXYLJ-UHFFFAOYSA-N propan-2-yl 2-[chlorosulfanyl-(2-oxo-2-propan-2-yloxyethyl)amino]acetate Chemical compound CC(C)OC(=O)CN(SCl)CC(=O)OC(C)C RSNAEYGESKXYLJ-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RDJUHLUBPADHNP-UHFFFAOYSA-N 1,2,3,5-tetrahydroxybenzene Chemical compound OC1=CC(O)=C(O)C(O)=C1 RDJUHLUBPADHNP-UHFFFAOYSA-N 0.000 description 1
- DFHOMHMJYXSIRC-UHFFFAOYSA-N 2-(butan-2-ylamino)-2-methylbutanoic acid Chemical compound CCC(C)NC(C)(CC)C(O)=O DFHOMHMJYXSIRC-UHFFFAOYSA-N 0.000 description 1
- BVAUMRCGVHUWOZ-UHFFFAOYSA-N 2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)C(C)NC1CCCCC1 BVAUMRCGVHUWOZ-UHFFFAOYSA-N 0.000 description 1
- RTVSUZHDJGUDGX-UHFFFAOYSA-N 2-(ethoxycarbonylamino)acetic acid Chemical compound CCOC(=O)NCC(O)=O RTVSUZHDJGUDGX-UHFFFAOYSA-N 0.000 description 1
- MZNHGIICBOOWBS-UHFFFAOYSA-N 2-methyl-2-(2-methylpropylamino)butanoic acid Chemical compound CCC(C)(C(O)=O)NCC(C)C MZNHGIICBOOWBS-UHFFFAOYSA-N 0.000 description 1
- SEWKCTGKOCOMQC-UHFFFAOYSA-N 2-methyl-2-(3-methylbutylamino)butanoic acid Chemical compound CCC(C)(C(O)=O)NCCC(C)C SEWKCTGKOCOMQC-UHFFFAOYSA-N 0.000 description 1
- BGCRFGMFNUMUQY-UHFFFAOYSA-N 2-methyl-2-(propan-2-ylamino)butanoic acid Chemical compound CCC(C)(C(O)=O)NC(C)C BGCRFGMFNUMUQY-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- SEXSQXSZCUQVBD-UHFFFAOYSA-N 4-ethyl-2-methyl-2-(propan-2-ylamino)octanoic acid Chemical compound CCCCC(CC)CC(C)(C(=O)O)NC(C)C SEXSQXSZCUQVBD-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- MBQNUYHHRXSELM-UHFFFAOYSA-N CC(=O)ON(C1CCCCC1)OC(=O)C Chemical compound CC(=O)ON(C1CCCCC1)OC(=O)C MBQNUYHHRXSELM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BUUGCEHIDSIHJB-UHFFFAOYSA-N [2-cyanoethyl(propan-2-yl)amino] thiohypochlorite Chemical compound CC(C)N(SCl)CCC#N BUUGCEHIDSIHJB-UHFFFAOYSA-N 0.000 description 1
- AKKUCDJYQINAHQ-UHFFFAOYSA-N [acetyloxy(propan-2-yl)amino] acetate Chemical compound CC(=O)ON(C(C)C)OC(C)=O AKKUCDJYQINAHQ-UHFFFAOYSA-N 0.000 description 1
- UXLYEJGCYZAZDX-UHFFFAOYSA-N [bis(2-cyanoethyl)amino] thiohypochlorite Chemical compound N#CCCN(SCl)CCC#N UXLYEJGCYZAZDX-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HVNPFQOMBNYVMB-UHFFFAOYSA-N butyl 2-(methylamino)acetate Chemical compound CCCCOC(=O)CNC HVNPFQOMBNYVMB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- YXAAPRUUUWQFGV-UHFFFAOYSA-N cyclohexyl 2-[chlorosulfanyl-(2-cyclohexyloxy-2-oxoethyl)amino]acetate Chemical compound C1CCCCC1OC(=O)CN(SCl)CC(=O)OC1CCCCC1 YXAAPRUUUWQFGV-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- TZJRPKDPYLAMJZ-UHFFFAOYSA-N ethyl 2-(4-methoxyanilino)acetate Chemical compound CCOC(=O)CNC1=CC=C(OC)C=C1 TZJRPKDPYLAMJZ-UHFFFAOYSA-N 0.000 description 1
- YZPXDEXTKPFTGC-UHFFFAOYSA-N ethyl 2-(butylamino)propanoate Chemical compound CCCCNC(C)C(=O)OCC YZPXDEXTKPFTGC-UHFFFAOYSA-N 0.000 description 1
- SMCWSSXGNIYYOL-UHFFFAOYSA-N ethyl 2-(chlorosulfanylamino)acetate Chemical compound C(C(=O)OCC)NSCl SMCWSSXGNIYYOL-UHFFFAOYSA-N 0.000 description 1
- NHRFJPKXIYYFMX-UHFFFAOYSA-N ethyl 2-(cyclohexylamino)acetate Chemical compound CCOC(=O)CNC1CCCCC1 NHRFJPKXIYYFMX-UHFFFAOYSA-N 0.000 description 1
- ORKAHUKYJCNDDI-UHFFFAOYSA-N ethyl 2-(ethoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OCC ORKAHUKYJCNDDI-UHFFFAOYSA-N 0.000 description 1
- OMECLFTURFUIIJ-UHFFFAOYSA-N ethyl 2-(ethoxycarbonylamino)propanoate Chemical compound CCOC(=O)NC(C)C(=O)OCC OMECLFTURFUIIJ-UHFFFAOYSA-N 0.000 description 1
- NRMPJIHWGVBZBB-UHFFFAOYSA-N ethyl 2-(ethylamino)acetate Chemical compound CCNCC(=O)OCC NRMPJIHWGVBZBB-UHFFFAOYSA-N 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- KHRLPZJTPHCMSQ-UHFFFAOYSA-N ethyl 2-(methylamino)propanoate Chemical compound CCOC(=O)C(C)NC KHRLPZJTPHCMSQ-UHFFFAOYSA-N 0.000 description 1
- CWPWNWCAOJRJJT-UHFFFAOYSA-N ethyl 2-(phenoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OC1=CC=CC=C1 CWPWNWCAOJRJJT-UHFFFAOYSA-N 0.000 description 1
- ROGQHXXFNVNMSC-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)acetate Chemical compound CCOC(=O)CNC(C)C ROGQHXXFNVNMSC-UHFFFAOYSA-N 0.000 description 1
- JBIONIMUHCHUOW-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)C JBIONIMUHCHUOW-UHFFFAOYSA-N 0.000 description 1
- XKFRTCBBCLBPOA-UHFFFAOYSA-N ethyl 2-(propanoylamino)acetate Chemical compound CCOC(=O)CNC(=O)CC XKFRTCBBCLBPOA-UHFFFAOYSA-N 0.000 description 1
- GSHWWBSVIZYONT-UHFFFAOYSA-N ethyl 2-[(2-chloroacetyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CCl GSHWWBSVIZYONT-UHFFFAOYSA-N 0.000 description 1
- XYVZUPHHGNHQHN-UHFFFAOYSA-N ethyl 2-[(4-chlorobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(Cl)C=C1 XYVZUPHHGNHQHN-UHFFFAOYSA-N 0.000 description 1
- XRIZQNOCVIQTRX-UHFFFAOYSA-N ethyl 2-[chlorosulfanyl(ethoxycarbonyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)C(=O)OCC XRIZQNOCVIQTRX-UHFFFAOYSA-N 0.000 description 1
- MLSGRWDEDYJNER-UHFFFAOYSA-N ethyl 2-anilinoacetate Chemical compound CCOC(=O)CNC1=CC=CC=C1 MLSGRWDEDYJNER-UHFFFAOYSA-N 0.000 description 1
- PTXRQIPIELXJFH-UHFFFAOYSA-N ethyl 2-benzamidoacetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1 PTXRQIPIELXJFH-UHFFFAOYSA-N 0.000 description 1
- AHGQESFVDCNOGJ-UHFFFAOYSA-N ethyl n-(cyanomethyl)carbamate Chemical compound CCOC(=O)NCC#N AHGQESFVDCNOGJ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-L iminodiacetate Chemical compound [O-]C(=O)CNCC([O-])=O NBZBKCUXIYYUSX-UHFFFAOYSA-L 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JHESHOHUMIZHMB-UHFFFAOYSA-N methyl 2-(ethoxycarbonylamino)acetate Chemical compound CCOC(=O)NCC(=O)OC JHESHOHUMIZHMB-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011493 spray foam Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4778581 | 1981-03-30 | ||
| JP56047785A JPS57163360A (en) | 1981-03-30 | 1981-03-30 | Bis(alkoxycarbonylmethyl)aminosulphenyl chloride derivative and its preparation |
| JP7852981 | 1981-05-22 | ||
| JP7852981A JPS57193472A (en) | 1981-05-22 | 1981-05-22 | Preparation of carbamate compound |
| JP17792981A JPS5877860A (ja) | 1981-11-05 | 1981-11-05 | アミノスルフエニルクロリド誘導体及びその製造法 |
| JP17792881 | 1981-11-05 | ||
| JP17792881A JPS5877878A (ja) | 1981-11-05 | 1981-11-05 | カ−バメイト化合物の製造法 |
| JP17792981 | 1981-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8201290A true NL8201290A (nl) | 1982-10-18 |
Family
ID=27462100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8201290A NL8201290A (nl) | 1981-03-30 | 1982-03-29 | Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4421693A (el) |
| KR (1) | KR880002299B1 (el) |
| AR (1) | AR230833A1 (el) |
| AU (1) | AU545481B2 (el) |
| CA (1) | CA1188706A (el) |
| CH (1) | CH653016A5 (el) |
| DD (2) | DD204251A5 (el) |
| DE (1) | DE3211087C2 (el) |
| ES (2) | ES8308539A1 (el) |
| FR (1) | FR2502616B1 (el) |
| GB (1) | GB2096994B (el) |
| GR (1) | GR75920B (el) |
| IL (1) | IL65384A (el) |
| IN (1) | IN156106B (el) |
| IT (1) | IT1147830B (el) |
| MA (1) | MA19424A1 (el) |
| MX (1) | MX160562A (el) |
| NL (1) | NL8201290A (el) |
| NZ (1) | NZ200163A (el) |
| SE (1) | SE456578B (el) |
| TR (1) | TR21303A (el) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5988461A (ja) * | 1982-11-11 | 1984-05-22 | Otsuka Chem Co Ltd | カ−バメイト系殺虫剤 |
| US4587353A (en) * | 1983-08-23 | 1986-05-06 | Ciba-Geigy Corporation | Process for producing N-chlorosulfenyl compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2649470A (en) * | 1951-10-10 | 1953-08-18 | Monsanto Chemicals | Cyanoalkyl substituted amine sulfides |
| US2766236A (en) * | 1954-02-25 | 1956-10-09 | Monsanto Chemicals | Preparing n-thioamines |
| US3843689A (en) * | 1970-11-09 | 1974-10-22 | Chevron Res | N-chlorothio carbamates |
-
1982
- 1982-03-24 CA CA000399286A patent/CA1188706A/en not_active Expired
- 1982-03-25 US US06/361,931 patent/US4421693A/en not_active Expired - Lifetime
- 1982-03-25 DE DE3211087A patent/DE3211087C2/de not_active Expired - Fee Related
- 1982-03-26 AR AR288882A patent/AR230833A1/es active
- 1982-03-27 ES ES510885A patent/ES8308539A1/es not_active Expired
- 1982-03-29 GB GB8209194A patent/GB2096994B/en not_active Expired
- 1982-03-29 MX MX192032A patent/MX160562A/es unknown
- 1982-03-29 NL NL8201290A patent/NL8201290A/nl not_active Application Discontinuation
- 1982-03-29 IT IT48109/82A patent/IT1147830B/it active
- 1982-03-29 SE SE8202001A patent/SE456578B/sv not_active IP Right Cessation
- 1982-03-29 NZ NZ200163A patent/NZ200163A/en unknown
- 1982-03-29 CH CH1915/82A patent/CH653016A5/fr not_active IP Right Cessation
- 1982-03-29 GR GR67741A patent/GR75920B/el unknown
- 1982-03-30 MA MA19629A patent/MA19424A1/fr unknown
- 1982-03-30 IL IL65384A patent/IL65384A/xx not_active IP Right Cessation
- 1982-03-30 KR KR8201384A patent/KR880002299B1/ko active
- 1982-03-30 IN IN354/CAL/82A patent/IN156106B/en unknown
- 1982-03-30 AU AU82143/82A patent/AU545481B2/en not_active Ceased
- 1982-03-30 TR TR21303A patent/TR21303A/xx unknown
- 1982-03-30 DD DD82238568A patent/DD204251A5/de not_active IP Right Cessation
- 1982-03-30 DD DD82246179A patent/DD208803A5/de not_active IP Right Cessation
- 1982-03-30 FR FR8205475A patent/FR2502616B1/fr not_active Expired
-
1983
- 1983-03-31 ES ES521601A patent/ES521601A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| KR830009018A (ko) | 1983-12-17 |
| AU545481B2 (en) | 1985-07-18 |
| AR230833A1 (es) | 1984-07-31 |
| IL65384A0 (en) | 1982-05-31 |
| KR880002299B1 (ko) | 1988-10-22 |
| GB2096994A (en) | 1982-10-27 |
| CA1188706A (en) | 1985-06-11 |
| IN156106B (el) | 1985-05-18 |
| CH653016A5 (fr) | 1985-12-13 |
| SE456578B (sv) | 1988-10-17 |
| AU8214382A (en) | 1982-10-07 |
| US4421693A (en) | 1983-12-20 |
| MA19424A1 (fr) | 1982-10-01 |
| DE3211087A1 (de) | 1982-11-18 |
| GB2096994B (en) | 1985-04-24 |
| IT8248109A0 (it) | 1982-03-29 |
| MX160562A (es) | 1990-03-23 |
| IL65384A (en) | 1985-10-31 |
| GR75920B (el) | 1984-08-02 |
| ES8405781A1 (es) | 1984-07-01 |
| DD208803A5 (de) | 1984-04-11 |
| SE8202001L (sv) | 1982-11-09 |
| ES510885A0 (es) | 1983-10-01 |
| TR21303A (tr) | 1984-03-22 |
| DD204251A5 (de) | 1983-11-23 |
| FR2502616B1 (fr) | 1986-09-05 |
| DE3211087C2 (de) | 1994-09-08 |
| NZ200163A (en) | 1985-08-16 |
| FR2502616A1 (fr) | 1982-10-01 |
| IT1147830B (it) | 1986-11-26 |
| ES8308539A1 (es) | 1983-10-01 |
| ES521601A0 (es) | 1984-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8201290A (nl) | Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. | |
| JPS5835182B2 (ja) | 硫黄含有化合物の製法 | |
| GB2058071A (en) | N-aryl-N-acyl-3-amino-oxazolidin- 2-one fungicides | |
| EP0016590B1 (en) | N-sulfinyl carbamates, their use as pesticides, pesticidal compositions containing them, methods of producing them and halosulfinyl carbamates formed during their production | |
| CH650250A5 (fr) | Carbamates, procede pour leur preparation et compositions insecticide, miticide ou nematocide les contenant. | |
| CA1170662A (en) | Carbamate derivatives, process for preparing same and carbamate insecticides | |
| US4394383A (en) | N-Alkoxysulfenylcarbamates useful as insecticides | |
| US4222938A (en) | Preparation of thiolcarbamates | |
| US4464387A (en) | Insecticidal phenyl hydantoin compounds | |
| JPS5936994B2 (ja) | Ｎ−スルフイニルカルバメ−ト | |
| EP0015749A1 (en) | Phosphoramidothioates, process for preparing them and insecticidal compositions containing them | |
| GB2084134A (en) | Insecticidal, miticidal and nematocidal dihydrobenzofuran aminosulphenyl carbabates | |
| US4229578A (en) | Process for preparing thioesters | |
| JPH0439464B2 (el) | ||
| HU198463B (en) | Process for producing carbamate derivatives with insecticidal effect | |
| NZ209827A (en) | Process for the preparation of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl n-(n,n-disubstituted aminosulphenyl)-n-methyl carbamate derivatives | |
| KR850000743B1 (ko) | 카바메이트유도체의 제조방법 | |
| JPH0216307B2 (el) | ||
| US4353908A (en) | Selected 2-trichloromethyl-4-pyrimidinyl carbonates and their use as fungicides | |
| JP2614108B2 (ja) | スルフェニルオキシムカーバメート誘導体の製造方法 | |
| JPH0717985A (ja) | 環状有機スズスルフィドと環状ジチオスルフィットおよびその製造法 | |
| JPH0368858B2 (el) | ||
| JPH0473427B2 (el) | ||
| JPH0124143B2 (el) | ||
| JPH031301B2 (el) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |